Hiring a Sales Leader (Part II): Running the Right Process

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This series outlines best practices to find and recruit a top-notch sales leader for your company, in three parts:

Read on for insights on making the best leadership hire for your company's needs.

Making your first sales leader hire is one of the most important things you will do as a founder or CEO of a ScaleUp. Many founders lead sales during the early stages of their company, but as they grow, they realize that they need an experienced leader to not only “carry the bag”   but to build, empower, and scale a team of sales reps for success.  
 
In Part I of this series, we walked you through the common pitfalls hiring managers to make when hiring a sales leader. Now, we’ll outline the five key steps hiring teams should take to establish a smooth hiring process that results in hiring the right sales leader for their team.  
 
While the focus of this piece is on hiring a sales leader, most of this content can be applied to almost all your senior hires.  
 
Step 1: Figure out what you need.  
 
Much like buying a house with your spouse, it’s critical that you align upfront with key stakeholders on what you are looking for when searching for candidates. Make sure you sit down with the necessary leaders (such as your co-founder, board, etc.) to agree on what competencies are a must for your sales leader.  
 
Often, founders note they prefer to meet candidates as a way to figure out what they want. While this can help you gather valuable information, you also have to remember that every conversation you have with a candidate is giving the market an impression of you and your business. If a candidate expects a formal interview and you haven’t defined your criteria, you and your organization risk seeming unprepared or indecisive.  
 
Instead, as the CEO or hiring manager, you should be able to clearly articulate what you are expecting out of this sales leader prior to meeting candidates. You want to come across as an articulate, thoughtful, and introspective leader from the outset, as this will make a huge impact on the candidate’s experience with your organization. 
 
Writing a scorecard is an effective way to clearly define and stack-rank the 5-8 core competencies you are looking for in a sales leader. This takes you beyond writing a simple position description to creating a tool that helps facilitate more focused, effective interviews. A clear scorecard also helps you assess candidates in a consistent way, helping you get an apples-to-apples view of candidates so that you can make decisions based on the key skills you’ve identified that are needed to be successful in the role.  
 
Step 2: Figure out how you will run your search.  
 
You will need to decide whether you want to self-source candidates or partner with external recruiters (be it retained or contingent recruiting services).  
 
If you decide to self-source candidates, it is important that the hiring manager takes full ownership of your search. This means taking initial meetings with candidates, as well as staying visible to the candidates throughout the process. While this is time-consuming, it is the #1 behavior – based on data from over a thousand Insight searches – that leads to better hiring outcomes.  
 
If you decide to leverage external recruiters, you will need to determine whether you prefer a retainer-based or contingent partnership.  
 
A retained search means you choose one vendor to exclusively run your search. Payment is on a retainer schedule, where the total fee is paid in installments. Payments typically occur in thirds in the U.S., but we have seen more variation in Europe & Israel. 
 
A contingent search means that firms are paid dependent on a hire. This model is often used for non-exec recruiting, and payment happens typically after an offer letter is signed.  
 
For executive hires including a true sales leader (or someone who reports to the CEO and leads your revenue business), Insight almost always recommends taking a retained approach. Contingent recruiting is more appropriate for hires below vice president, with some specific exceptions for high-impact roles, like a Director of Data Science. 
 
While self-sourcing candidates can be a huge cost saver, searches often take longer, outreach tends to be less research-driven and organized, and candidate quality can be lower. Inversely, recruiters tend to have better access to passive, best-in-market candidates and can provide these candidates at scale.  
 
In general, when hiring a sales leader, Insight recommends leveraging retained recruiters over self-sourcing candidates or using contingent recruiting services – especially as you look to grow your organization long term.  

Step 3: Clearly outline your interview process.  
 
As companies scale, leaders juggle many different priorities. It’s exciting and sometimes chaotic. One thing that should not be chaotic is your hiring and interview process for executives. Lacking a clear interview process shows that your business doesn’t prioritize the hire or the candidate experience, which will repel the best candidates.  
 
ScaleUps can easily impress leaders by showing their commitment to recruiting the best talent by simply being organized, thoughtful, and planned about the hiring experience. It’s not rocket science, but it’s a step that is often overlooked. 
 
We recommend designing an intentional interview process with a maximum of 4-7 company-led interviews following the recruiter call. Ideally, this is a tight process with 4-5 interview rounds (including recruiter vetting) and only a few business days between rounds. Your interview process should consist of the following: 
 

  • Recruiter vetting. The recruiter should be at the top of the funnel, reaching out to prospects, validating their background, strengths, and weaknesses, and deciding who then meets with the company.  
  • CEO or hiring manager takes the first call after the recruiter. This call should last for at least an hour, and the hiring manager should spend at least 50% of the time selling candidates. Remember, the best candidates are passive & busy; they want to be sold on your vision and it’s difficult for them to get excited about your company if that vision is not shared with them from the very beginning.  
  • One or two hard assessment rounds, which can include a work exercise or assignment. These are competency-based interviews, facilitated by the scorecard. Ideally, these interviews are led by members of the leadership team or other senior people (such as a board member or advisor) who are qualified to assess a candidate’s fit for the role. We recommend that each interviewer be assigned only 2-4 competencies to evaluate a candidate. They should then share their assessment of the candidate with one central person before the candidate speaks to any of the other interviewers. This removes bias in the feedback and helps give a clearer view of the candidate for group discussion.  
  • Work exercise or assignment. If you choose to include an exercise as part of your 1-2 hard assessment rounds, do so after the candidate has had the time to learn the business. Most of our portfolio companies incorporate an exercise to understand how the candidate processes information and unpacks problems. This should be time-contained so that the candidate doesn’t feel like they are doing free work. These exercises can take many forms, but we recommend using one focused on how the candidate thinks and works, rather than one focused on identifying the “right” answer.  
  •  Sales and culture fit assessment rounds. During the second half of the interview process, we recommend spending more time assessing culture. Remember, the key is to find someone who will be a “culture add,” not just a “fit.” This will allow you to think about developing your culture rather than just hiring people who look and sound like the people who are already a part of your team.  

 
Step 4: Align on the questions you will ask candidates. 

 
We recommend asking open-ended questions that will give you a better understanding of how the individual operates. For example, instead of asking whether the candidate manages a forecasting and pipeline review process (which could be answered with a yes or no), ask how they ensure the accuracy of their monthly or quarterly forecast.  
 
Questions should focus on a few key areas such as their background, Go-to-Market skills, Metrics and Process drivers, Core Selling skills, and Team-Building. Drive the discussion to ensure that you’re covering all these key areas. Understanding their past roles is important, but what you’re really trying to assess is their capability of running your sales organization now.  
 
A few sample questions are: 
 

  • Give us the 5-minute overview of your background – how did you get here and why are you considering leaving your current role? 
  • What’s the one thing that your past organizations would say about how you run your sales organization? 
  • What are the KPIs that you use to manage your business?  
  • What are some red flags that indicate that your process isn’t working? And how would you go about making adjustments? 
  • Walk me through your current organization’s sales process – how large are the deals and who are you selling to? What steps does your team follow? 
  • What are one or two things that you’ve done in building out teams that you wish, in hindsight, you would have done differently? 

 
The goal of these sessions is to determine if this person has the skills and is the right cultural fit for your organization for right now. For the pitfalls to avoid when hiring, please read our last blog. 
 

Step 5: Close the candidate.  
 
Executives will expect a level of sophistication throughout the entire search process, and this includes how they are closed.  
 
As a hiring manager, you should think about closing a candidate throughout the process, as you want to ensure a good fit on both sides – and you want to avoid any last-minute surprises. Make sure you are setting expectations, asking key questions about their wants/needs, and getting the right stakeholders brought in internally to be sure you have their backing. Often CEOs need to get board approval before making an executive hire, so it’s best to preview the hire and get buy-in early from your board to ensure you can offer the right package. 
 
Additionally, it can often be easier to close a candidate when partnering with a good recruiter, as they can help you ensure alignment with your candidate’s requirements throughout the process. They typically ask a candidate critical questions early, such as: What are location needs/ limitations, what days would they want to work from home (a newer theme stemming from COVID-19), and what are their compensation expectations? This information-sharing is critical to ultimately win the best talent. 
 
So, how should you officially close a candidate? 
 
When you are ready to go to offer, come ready with a number. Do not put anything on paper during these discussions. Spend the bulk of your time orally discussing the big numbers (i.e., base, bonus, equity) with a candidate until you agree on the final offer. Once that is settled, you can then send the paperwork. From there, it should hopefully be a straightforward process getting the offer signed.  
 
While this intentional hiring process takes a lot of time and care, we’ve seen that emphasizing these processes and disciplines is worth the initial investment. At Insight, a trap we’ve seen founders fall into over and over again is underestimating the time and attention it takes to hire an executive team. As founders mature, they learn the value of this time investment, because early leadership hires super-charge ScaleUps to the next stage of massive growth.  
 
Like setting up a finance function or building a scalable enterprise product, putting in the right processes and structure will increase your chances of success long term. 
 
For more insight into executive hiring practices, please contact the Talent and the Sales & Customer Success Center of Excellence. 

Hiring a Sales Leader (Part III): What Level Should I Hire For?

In the next part of the series, we will answer one of the most common questions we get around hiring a sales leader: what level should I hire for?”
  • Helen Hua

    Helen Hua, Senior Vice President, Talent COE

    Helen joined Insight in 2017 to lead executive networking, best practices and other executive talent initiatives across the Insight portfolio. Prior, Helen was a Principal at True Search, an international executive search firm. At True, she led and drove executive searches across scaling venture and private-equity backed technology companies…
  • Travis Kassay, Executive Vice President, Sales & CS COE

    Travis joined Insight in 2019 as an EVP on the Insight Onsite team. Travis partners with portfolio company CEOs and their leadership teams to build scalable and effective go-to-market strategies. Leveraging his more than 20 years of experience in sales, inside sales, and sales operations, Travis consults with portfolio companies to address…